Triethylamine → 2-(2-Acetylsulfanyl-acetylamino)-succinic acid 4-tert-butyl ester

HRID 895969Notes

Reaction equation

HRID 895969 reaction equation
FC1C(O[C:9](=[O:15])[CH2:10][S:11][C:12](=[O:14])[CH3:13])=C(F)C(F)=C(F)C=1F.[NH2:20][C@H:21]([C:30]([OH:32])=[O:31])[CH2:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26].C(N(CC)CC)C>ClCCl>[C:25]([O:24][C:23](=[O:29])[CH2:22][CH:21]([NH:20][C:9](=[O:15])[CH2:10][S:11][C:12](=[O:14])[CH3:13])[C:30]([OH:32])=[O:31])([CH3:28])([CH3:26])[CH3:27]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 3569623S-Acetylthioglycolic acid pentafluorophenyl esterHCID 70105704-tert-Butyl hydrogen L-aspartate

Product 1

HCID 235971832-(2-Acetylsulfanyl-acetylamino)-succinic acid 4-tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Acetylsulfanyl-acetic acid pentafluorophenyl ester (1.6 g, 5.3 mmol) and H-Asp(OtBu)—OH (1 g, 5.3 mmol) were mixed in 20 ml of dry dichloromethane (DCM). Then 1.6 ml of triethylamine (11.5 mmol) was added, and the reaction was allowed to proceed at ambient temperature for 3.5 hours. The organic layer was then extracted with 3×15 ml of 1 M sodium carbonate, the combined aqueous fractions were acidified with 100 ml of 1 M sodium hydrogensulfate and extracted with 3×30 ml ethyl acetate. The combined organic fractions were then rinsed with 30 ml of 1 M sodium hydrogensulfate, 30 ml of 5 M NaCl, dried over sodium sulfate, filtered, and evaporated under reduced pressure to yield 1.97 g of a nearly colorless syrup which was used without further purification. MW=305 (found 306, M+1).

Workup

  1. extractionThe organic layer was then extracted with 3×15 ml of 1 M sodium carbonate
  2. extractionextracted with 3×30 ml ethyl acetate
  3. washThe combined organic fractions were then rinsed with 30 ml of 1 M sodium hydrogensulfate, 30 ml of 5 M NaCl
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customto yield 1.97 g of a nearly colorless syrup which
  8. customwas used without further purification

Sources & evidence

ORD record
ord-c4f152f16ca046bbab9e99a1710031c8
Source dataset
uspto-grants-2005_07
Patent number
US06919178B2

Reaction notes

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